Ferrocenecarboxylic acid

Ferrocenecarboxylic acid
Names
	IUPAC name Ferrocenecarboxylic acid
	Other names FcCO2H, Ferrocenemonocarboxylic acid, Ferrocenic acid
Identifiers
CAS Number	1271-42-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	26585892;
PubChem CID	15764230;
	InChI InChI=1S/C6H5O2.C5H5.Fe/c7-6(8)5-3-1-2-4-5;1-2-4-5-3-1;/h1-4H,(H,7,8);1-5H;/q2*-1;+2 Key: BAJHDUZEIKRKAS-UHFFFAOYSA-N;
	SMILES [CH-]1C=CC=C1.C1=C[C-](C=C1)C(=O)O.[Fe+2];
Properties
Chemical formula	C11H10FeO2
Molar mass	230.044 g·mol−1
Appearance	yellow solid
Density	1.862 g/cm3
Melting point	214–216 °C (417–421 °F; 487–489 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Ferrocenecarboxylic acid is the organoiron compound with the formula (C
5H
5)Fe(C
5H
4CO
2H). It is the simplest carboxylic acid derivative of ferrocene. It can be prepared in two steps from ferrocene by acylation with a 2-chlorobenzoyl chloride followed by hydrolysis.^[2]

On a two-dimensional surface, most carboxylic acids form hydrogen-bonded dimers. Ferrocenecarboxylic acid instead forms a mixture of dimers and cyclic pentamers and organizes into a quasicrystalline order with fivefold symmetry, the first known molecular quasicrystal.^[3]

Reactions and derivatives

The pK_a of ferrocenecarboxylic acid is 7.79±0.08. The acidity increases more than a thousand-fold, to 4.54±0.04 upon oxidation to the ferrocenium cation.^[4]

By treatment with thionyl chloride, the carboxylic acid anhydride ([(C
5H
5)Fe(C
5H
4CO)]
2O) is produced.^[5]^[6]

Derivatives of ferrocenecarboxylic acid are components of some redox switches.

Related compounds

1,1'-Ferrocenedicarboxylic acid
Ferrocenecarboxaldehyde

References

↑ Lin, Lily; Berces, Attila; Kraatz, Heinz-Bernhard (1998). "Ferrocenic Acid Derivatives: Towards Rationalizing Changes in the Electronic and Geometric Structures". Journal of Organometallic Chemistry 556 (1–2): 11–20. doi:10.1016/S0022-328X(97)00785-7.
↑ Perry C. Reeves (1977). "Carboxylation of Aromatic Compounds: Ferrocenecarboxylic Acid". Organic Syntheses 56: 28. doi:10.15227/orgsyn.056.0028.
↑ Wasio, Natalie A.; Quardokus, Rebecca C.; Forrest, Ryan P.; Lent, Craig S.; Corcelli, Steven A.; Christie, John A.; Henderson, Kenneth W.; Kandel, S. Alex (March 2014). "Self-assembly of hydrogen-bonded two-dimensional quasicrystals". Nature 507 (7490): 86–89. doi:10.1038/nature12993.
↑ Fabbrizzi, Luigi (2020). "The Ferrocenium/Ferrocene Couple: A Versatile Redox Switch". Chemtexts 6 (4). doi:10.1007/s40828-020-00119-6.
↑ Tazi, Mehdi; Roisnel, Thierry; Mongin, Florence; Erb, William (2017). "Ferrocenecarboxylic Anhydride: Identification of a New Polymorph". Acta Crystallographica Section C Structural Chemistry 73 (10): 760–766. doi:10.1107/S205322961701124X. PMID 28978780. https://hal-univ-rennes1.archives-ouvertes.fr/hal-01617956/file/Ferrocenecarboxylic%20anhydride%20-HAL.pdf.
↑ Lau, Hans; Hart, Harold (1959). "Notes- Preparation and Hydrolysis of Crystalline Ferrocenoyl Chloride". The Journal of Organic Chemistry 24 (2): 280–281. doi:10.1021/jo01084a647.

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Ferrocenecarboxylic acid. Read more

[1] Lin, Lily; Berces, Attila; Kraatz, Heinz-Bernhard (1998). "Ferrocenic Acid Derivatives: Towards Rationalizing Changes in the Electronic and Geometric Structures". Journal of Organometallic Chemistry 556 (1–2): 11–20. doi:10.1016/S0022-328X(97)00785-7.

[2] Perry C. Reeves (1977). "Carboxylation of Aromatic Compounds: Ferrocenecarboxylic Acid". Organic Syntheses 56: 28. doi:10.15227/orgsyn.056.0028.

[3] Wasio, Natalie A.; Quardokus, Rebecca C.; Forrest, Ryan P.; Lent, Craig S.; Corcelli, Steven A.; Christie, John A.; Henderson, Kenneth W.; Kandel, S. Alex (March 2014). "Self-assembly of hydrogen-bonded two-dimensional quasicrystals". Nature 507 (7490): 86–89. doi:10.1038/nature12993.

[4] Fabbrizzi, Luigi (2020). "The Ferrocenium/Ferrocene Couple: A Versatile Redox Switch". Chemtexts 6 (4). doi:10.1007/s40828-020-00119-6.

[5] Tazi, Mehdi; Roisnel, Thierry; Mongin, Florence; Erb, William (2017). "Ferrocenecarboxylic Anhydride: Identification of a New Polymorph". Acta Crystallographica Section C Structural Chemistry 73 (10): 760–766. doi:10.1107/S205322961701124X. PMID 28978780. https://hal-univ-rennes1.archives-ouvertes.fr/hal-01617956/file/Ferrocenecarboxylic%20anhydride%20-HAL.pdf.

[6] Lau, Hans; Hart, Harold (1959). "Notes- Preparation and Hydrolysis of Crystalline Ferrocenoyl Chloride". The Journal of Organic Chemistry 24 (2): 280–281. doi:10.1021/jo01084a647.

[1]

[2]

[3]

[4]

[5]

[6]

Names

IUPAC name Ferrocenecarboxylic acid
Other names FcCO₂H, Ferrocenemonocarboxylic acid, Ferrocenic acid
Identifiers
CAS Number	1271-42-7^Y
3D model (JSmol)	Interactive image
ChemSpider	26585892
PubChem CID	15764230
InChI InChI=1S/C6H5O2.C5H5.Fe/c7-6(8)5-3-1-2-4-5;1-2-4-5-3-1;/h1-4H,(H,7,8);1-5H;/q2*-1;+2 Key: BAJHDUZEIKRKAS-UHFFFAOYSA-N
SMILES [CH-]1C=CC=C1.C1=C[C-](C=C1)C(=O)O.[Fe+2]
Properties
Chemical formula	C₁₁H₁₀FeO₂
Molar mass	230.044 g·mol⁻¹
Appearance	yellow solid
Density	1.862 g/cm³^[1]
Melting point	214–216 °C (417–421 °F; 487–489 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ferrocenecarboxylic acid

Topic: Chemistry

Reactions and derivatives

Related compounds

References